


Oh, Oh, Wouldn't He Be Delicious

by orphan_account



Category: Critical Role (Web Series)
Genre: Crossdressing, F/M, Maids, might be a bit mature but not by a lot i think
Language: English
Status: Completed
Published: 2020-04-19
Updated: 2020-04-19
Packaged: 2021-03-02 00:08:28
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 535
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23725852
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: The thing about being married to Jester was that there was nothing better in the world. A life that was once sad and lonely was now bright and beautiful full of laughter and surprises. That was the other thing about being married to Jester, Caleb never knew what was going to come next.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 1
Kudos: 23





	Oh, Oh, Wouldn't He Be Delicious

The thing about being married to Jester was that there was nothing better in the world. A life that was once sad and lonely was now bright and beautiful full of laughter and surprises. That was the other thing about being married to Jester, Caleb never knew what was going to come next.

Case in point, the outfit that laid on their bed. Caleb stared at it, hardly believing it. Jester had mentioned getting a little something to spice things up in the bedroom. It would certainly do that. Part of him was tempted to pretend he didn’t see it or just hide the thing, but that would just disappoint Jester. With a heavy sigh, Caleb put the outfit on.

Marriage was sometimes about making compromises to see your partner smile.

* * *

Jester excitedly skipped home. Her special outfit had finally came in and she couldn’t wait to surprise Caleb with it. She giggled as she opened the front door imagining the look on Caleb’s face when he saw it. “Caleb! I’m home!” Jester called out. There was no response, so she must’ve gotten home first which worked perfectly for her plans.

Humming, she made her way into their bedroom where her outfit was. Jester’d opened it earlier, but she didn’t have the chance to try it on yet. The only thing was that her new outfit wasn't on the bed. She may not have had the memory that Caleb had, but Jester was super certain that she knew where she had left it. "Now, where could it be?" Jester asked out loud to no one.

"Can I help you, Master?" Jester turned around confused. Caleb stood there fiddling with a feather duster completely beet red. He was also wearing Jester's new maid outfit. It was just as lacy and frilly as she was hoping for, but on Caleb, it had a completely different effect than Jester had intended. The neckline kept slipping off of Caleb's bony shoulders reminding Jester needed to put more weight on him. With his seven inches he had on her, the dress ended at mid-thigh on Caleb. Jester had to admit that the little headband did look adorable on him, but with his red hair, most hair accessories suited him well.

"Caleb?" Jester asked. She wasn't sure what to say about this.

Caleb managed to turn an even brighter shade of red. "I saw the outfit you got for me. Does it suit me," he gulped hard and added, "Master?"

"You found the dress I was going to wear," Jester said, fighting back a giggle. Caleb was already embarrassed enough without her laughing at him. Though, Jester had to admit that it would've been sexy if Caleb actually looked comfortable in it. He had a couple of dresses that he would wear on occasion that suited him well, but none of them showed off even half as much leg. “That was the surprise for you.”

"Oh, oh." He visibly relaxed. "So, I can take this off now?"

Jester allowed herself to laugh. "Of course! It looks terrible on you. In fact, I think it would look a lot better on the floor."

Caleb batted his eyelashes fighting a smirk. "Oh, Master."

**Author's Note:**

> I had this idea for over a year, but went oh no one would ever want to read this. Then people made comments on the widojest discord wanting Maid Caleb, so here we are.


End file.
